2-(4-chlorophenylsulfanyl)-3-oxobutyric Acid Methyl Ester → [8-chloro-3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266472Notes

Reaction equation

HRID 2266472 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([S:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:19](=O)[CH3:20]>O1CCOCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([S:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)=[C:19]([CH3:20])[NH:13]2

Participants

4

Reactant 2

HCID 125614692-(4-chlorophenylsulfanyl)-3-oxobutyric Acid Methyl EsterHCID 66717604Methyl 2-(3-amino-4-chlorophenoxy)acetate

Product 1

HCID 68783252[8-chloro-3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3-amino-4-chlorophenoxy)acetic acid methyl ester (2.1 g), 2-(4-chlorophenylsulfanyl)-3-oxobutyric acid methyl ester (2.5 g), polyphosphoric acid (10 g) and dioxane (30 mL) was heated at 130° C. for 2 days. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was diluted with water and the resulting precipitate collected by filtration, washed with water and dichloromethane and dried to afford title compound, 1.6 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed under reduced pressure
  3. additionThe residue was diluted with water
  4. filtrationthe resulting precipitate collected by filtration
  5. washwashed with water and dichloromethane
  6. customdried

Sources & evidence

ORD record
ord-753ce97bf4604866b564cc16b7da5d21
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

Loading…